Water → HCID 20029931, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (60% oil dispersion, 1.2 g, 0.03 mol) in DMF (20 ml) was added at 70° C. under N2 a solution 3 (37 g, 0.03 ml) in DMF (30 ml). After stirring for 15 minutes at 70° C. a solution of (S) 2 in DMF (50 ml) was added dropwise. After the addition, the mixture was heated at 120° C. for 18 hours. The solution was then poured into H2O and extracted with EtOAc (3×). The organic extracts were washed with H2O (2×), saturated NaCl (1×), dried, filtered and concentrated to dryness. The residue was treated with H2O (250 ml) and AcOH (25 ml) and stirred overnight at room temperature. The solution was extracted with EtOAc (2×), neutralized with saturated Na2CO3 and extracted with CHCl3 (9×). The organic extracts were dried, filtered and concentrated to yield 8.5 g of 4; 'H NMR (CDCl3) δ2.7 (6H, m), 3.8 (6H, s), 4.1 (3H, m), 6.7 (3H, bs), 6.95 (2H, d), 7.75 (2H, d). ##STR144##

Provenance & Evidence